[ CAS No. 57-67-0 ] {[proInfo.proName]}

Name: 57-67-0|4-Amino-N-carbamimidoylbenzenesulfonamide|98% (<8%H2O)
Brand: Ambeed
SKU: A293011
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Quality Control of [ 57-67-0 ]

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Product Details of [ 57-67-0 ]

CAS No. :	57-67-0	MDL No. :	MFCD00038136
Formula :	C₇H₁₀N₄O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BRBKOPJOKNSWSG-UHFFFAOYSA-N
M.W :	214.24	Pubchem ID :	5324
Synonyms :		Chemical Name :	4-Amino-N-carbamimidoylbenzenesulfonamide

Safety of [ 57-67-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 57-67-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 57-67-0 ]
Downstream synthetic route of [ 57-67-0 ]

[ 57-67-0 ] Synthesis Path-Upstream 1~19

1
[ 542-78-9 ]
[ 57-67-0 ]
[ 68-35-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium methylate In methanol at 65℃; for 2 h;	A mixing 8.6 g NH4Cl and 23. lg (NH4) 2C03 in a certain ratio, Adding activated carbon catalyst, Then add 32g of dicyandiamide heated to melt at 150 ° C for 30min; B To join the above Rong melt liquid 80g p-aminosulfonamide, 70g sodium carbonate continue to melt financial, in 25min heated to 150 ° C, to maintain 30min; C To the mixture obtained in step B, 400 ml of boiling water was added and the mixture was stirred well. The resulting suspension was cooled to 40 ° C and filtered to obtain crude sulfanilamide. To the flask, 93 g of a 25percent methanol solution of sodium methoxide, 33 g of crude sulfanilamide, Stirring to join malondialdehyde 13. 5g, heating to 65 ° C, reaction 2h, Complete ring condensation reaction, recovery of methanol after sulfadiazine crude. Add 200ml of water to the crude, heating, saturated with hydrogen peroxide to adjust the pH to 9. 5, after the whole solution, add 20g of activated carbon, heat decolorization at 80 ° C. Filtration, the filtrate added ‰ 5g ammonium chloride, with 10percent acetic acid to adjust the pH to 5.2. Precipitation crystal, cold after filtration, washing, drying Of the sulfadiazine quality, yield 89percent, purity of 98.0percent.

Reference： [1] Patent: CN105254575, 2016, A, . Location in patent: Paragraph 0015-0016

2
[ 7119-27-9 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1] Yakugaku Zasshi, 1951, vol. 71, p. 1349,1354[2] Chem.Abstr., 1952, p. 8033
[3] Patent: US2688015, 1952, ,
[4] Patent: US2693466, 1952, ,
[5] DRP/DRBP Org.Chem.,
[6] Patent: DE812316, 1950, ,

3
[ 5436-21-5 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1] Yakugaku Zasshi, 1951, vol. 71, p. 1349,1354[2] Chem.Abstr., 1952, p. 8033
[3] Yakugaku Zasshi, 1949, vol. 69, p. 477[4] Chem.Abstr., 1950, p. 3455
[5] Patent: DE871303, 1951, ,

4
[ 625-34-3 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1] Patent: CH242350, 1944, ,

5
[ 30845-73-9 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1] Patent: US2690439, 1953, ,

6
[ 53133-27-0 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1] Patent: DE951990, 1954, ,

7
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1] Yakugaku Zasshi, 1951, vol. 71, p. 1309,1312[2] Chem.Abstr., 1952, p. 8094

8
[ 123-54-6 ]
[ 57-67-0 ]
[ 57-68-1 ]

Reference： [1] Journal of the Chemical Society, 1945, p. 689,691
[2] Patent: CH239169, 1945, ,
[3] Journal of Pharmacology and Experimental Therapeutics, 1943, vol. 77, p. 127

9
[ 63913-41-7 ]
[ 57-67-0 ]
[ 57-68-1 ]

Reference： [1] Yakugaku Zasshi, 1951, vol. 71, p. 1309,1312[2] Chem.Abstr., 1952, p. 8094

10
[ 127099-85-8 ]
[ 63-74-1 ]
[ 57-67-0 ]

Reference： [1] Patent: CN105254575, 2016, A, . Location in patent: Paragraph 0015-0016

11
[ 63-74-1 ]
[ 127099-85-8 ]
[ 57-67-0 ]

Reference： [1] Nature (London, United Kingdom), 1941, vol. 148, p. 24
[2] Biochemical Journal, 1938, vol. 32, p. 1101,1109
[3] Patent: CH229792, 1942, ,
[4] Oriental Journal of Chemistry, 2011, vol. 27, # 2, p. 645 - 648

12
[ 113-00-8 ]
[ 121-57-3 ]
[ 57-67-0 ]

Reference： [1] Journal of Organic Chemistry, 1956, vol. 21, p. 1198

13
[ 39604-29-0 ]
[ 57-67-0 ]

Reference： [1] Patent: US2359363, 1942, ,
[2] Patent: US2359363, 1942, ,

14
[ 19077-97-5 ]
[ 57-67-0 ]

Reference： [1] Patent: CH231667, 1941, ,
[2] Doklady Akademii Nauk SSSR, 1942, vol. 36, p. 203[3] Chem.Abstr., 1943, p. 2722

15
[ 63-74-1 ]
[ 57-67-0 ]

Reference： [1] Journal of the Chemical Society, 1946, p. 491,494

16
[ 121-61-9 ]
[ 57-67-0 ]

Reference： [1] Patent: CH231667, 1941, ,

17
[ 4435-59-0 ]
[ 57-67-0 ]

Reference： [1] Patent: US2414403, 1945, ,

18
[ 718640-00-7 ]
[ 57-67-0 ]

Reference： [1] Patent: US2416995, 1942, ,
[2] Patent: CH236130, 1941, ,

19
[ 113-00-8 ]
[ 63-74-1 ]
[ 57-67-0 ]

Reference： [1] Journal of the Chemical Society, 1946, p. 491,494

[ 57-67-0 ] Synthesis Path-Downstream 1~88

1
4-(2-methyl-piperidino)-but-3-en-2-one [ No CAS ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1951,vol. 71,p. 1309,1312
Chem.Abstr.,1952,p. 8094

2
[ 90-02-8 ]
[ 57-67-0 ]
[ 16182-40-4 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 228
[2]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 511 - 516
[3]RSC Advances,2014,vol. 4,p. 39214 - 39225

3
[ 7119-27-9 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1951,vol. 71,p. 1349,1354
Chem.Abstr.,1952,p. 8033
[2]Patent: US2488081,1945,
DRP/DRBP Org.Chem.,
[3]Patent: DE812316,1950,

4
[ 1540-29-0 ]
[ 57-67-0 ]
sulfanilic acid-(5-butyl-4-methyl-6-oxo-1,6-dihydro-pyrimidin-2-ylamide) [ No CAS ]

Reference： [1]Proceedings - Indian Academy of Sciences, Section A,1942,vol. 16,p. 115,121

5
[ 625-34-3 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1]Patent: CH242350,1944,

6
[ 117-80-6 ]
[ 57-67-0 ]
[ 120983-26-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5576 - 5592
[2]Journal of the American Chemical Society,1950,vol. 72,p. 4804

7
[ 5436-21-5 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1951,vol. 71,p. 1349,1354
Chem.Abstr.,1952,p. 8033

8
[ 30845-73-9 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1]Patent: US2690439,1953,

9
[ 13706-86-0 ]
[ 57-67-0 ]
sulfanilic acid-(4-hydroxy-4-isobutyl-5-methyl-4<i>H</i>-imidazol-2-ylamide) [ No CAS ]

Reference： [1]Patent: US2523528,1949,

10
[ 53133-27-0 ]
[ 57-67-0 ]
[ 127-79-7 ]

Reference： [1]Patent: DE951990,1954,

11
[ 2010-06-2 ]
[ 57-67-0 ]
[ 85811-07-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With hydrogenchloride; sodium acetate; sodium nitrite; In ethanol; water; at 0 - 5℃; for 2h;	General procedure: A solution of aryl diazonium chloride was prepared by adding cold sodium nitrite solution (0.7 gin 10 mL H2O) to a cold suspension of aryl amine 2 and/or 3 (0.01 mol) in 3 mL concentrated HCl withstirring. The freshly prepared solution was added with continuous stirring to a cold solution (0-5 C) of 2-aminothiazole 1 (1 g, 0.01 mol) in 30 mL ethanol and 4.0 g sodium acetate. The reaction mixture was stirred at 0-5 C for 2 h, diluted with water, and the products collected by filtration. The obtained 2-amino-5-arylazothiazoles 4-7 were dried and recrystallized from ethanol.

Reference： [1]Molecules,2016,vol. 21
[2]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

12
[ 57634-55-6 ]
[ 57-67-0 ]
[ 103726-70-1 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

13
[ 842-74-0 ]
[ 57-67-0 ]
[ 78530-45-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 1093 - 1094
[2]Journal of the Indian Chemical Society,1981,vol. 58,p. 297 - 299

14
[ 1157-39-7 ]
[ 57-67-0 ]
[ 132184-52-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1727 - 1728

15
[ 56201-56-0 ]
[ 57-67-0 ]
C₁₉H₁₆N₄O₈S₂ [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1988,vol. 65,p. 422 - 426

16
[ 871-58-9 ]
[ 57-67-0 ]
2-guanidyl sulphamidophenyl-O-butyl xanthate [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 857 - 858

17
[ 84156-21-8 ]
[ 57-67-0 ]
[ 84158-46-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 449 - 453

18
2-(2-Benzyloxy-phenyl)-7-hydroxy-[1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one [ No CAS ]
[ 57-67-0 ]
C₂₅H₂₀N₈O₆S [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,1982,vol. 71,p. 178 - 182

19
[ 57-67-0 ]
[ 57198-80-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite; In water;Cooling;	General procedure: A solution of NaNO2 (0.4 g, 5.8 mole in 5 mL H2O) was added drop wise to a well cooled stirred solution of 4-aminobenzenesulfonic acid 2 (0.87 g, 0.005 mol), p-aminobenzenesulphonamide 3 (0.86 g, 0.00 5 mol), N-(4-aminophenylsulfonyl) acetamide 4 (1.07 g, 0.005 mol), 1-(4-aminophenylsulfonyl) guanidine 5 (1.07 g,0 .005 mol) and 4-amino-N-(4,6-dimethylpyrimidin-2-yl) benzenesulfonamide 6 (1.4 g, 0.005 mol) in a mixture of concentrated HCl (3 mL) and H2O (3 mL ). The above cooled diazonium solution was added slowly to a well stirred solution of curcumin 1 (1.84 g,0.005 mol) in pyridine (25 mL). The reaction was stirred for 2 h. The formed precipitate was filtered off, dried and crystallized from EtOH/benzene to give the sulpha derivatives 12, 13, 14, 15 and 16, respectively.

Reference： [1]Journal of the Indian Chemical Society,1998,vol. 75,p. 325 - 325
[2]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2010,vol. 77,p. 755 - 766
[3]Letters in drug design and discovery,2017,vol. 14,p. 1425 - 1432

20
[ 98-03-3 ]
[ 57-67-0 ]
thiophene-2-carbaldehyde sulphaguanidine [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 811 - 819
[2]Bulletin of the Polish Academy of Sciences: Chemistry,2000,vol. 48,p. 195 - 201
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2004,vol. 179,p. 227 - 236

21
[ 487-89-8 ]
[ 57-67-0 ]
4-[(1H-indol-3-yl)methylene]amino}-N-carbamimidoylbenzenesulfonamide [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 811 - 819
[2]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1189 - 1199
[3]Journal of Enzyme Inhibition and Medicinal Chemistry,2018,vol. 33,p. 629 - 638
[4]Bulletin of the Polish Academy of Sciences: Chemistry,2000,vol. 48,p. 195 - 201
[5]Journal of the Indian Chemical Society,2007,vol. 84,p. 197 - 199

22
[ 873-58-5 ]
[ 57-67-0 ]
C₁₂H₁₆N₆O₃S₃ [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2000,vol. 163,p. 219 - 251

23
[ 57-67-0 ]
[ 873-57-4 ]
C₁₃H₁₈N₆O₂S₃ [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2000,vol. 163,p. 219 - 251

24
[ 57-67-0 ]
piperazine dithiocarbamate sodium salt [ No CAS ]
C₁₂H₁₇N₇O₂S₃ [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2000,vol. 163,p. 219 - 251

25
[ 57-67-0 ]
[ 109-77-3 ]
C₁₀H₉N₇O₂S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6500 - 6509

26
[ 25784-91-2 ]
[ 57-67-0 ]
[ 372094-81-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 2,4-dichlorophenoxyacetic acid dimethylamine;	Example 106 N-[4-(Amidinoaminosulfonyl)phenyl]-(2-chloro-5-nitrophenyl)carboxamide The title compound (0.280 g, yield 70%) was obtained according to the procedure described in Example 2 using sulfaguanidine (a product of Sigma, 0.214 g, 1.0 mmol), DMA (2.5 ml) and 2-chloro-5-nitrobenzoyl chloride (0.242 g, 1.1 mmol). Rf 0.24 [methylenchloride:methanol=7:1 (v/v)]; 1H-NMR (400 MHz, DMSO-d6, TMS): delta(ppm) 6.70 (4H, br), 7.77 (2H, d, J=8.8 Hz), 7.81 (2H, d, J=8.8 Hz), 7.91 (1H, d, J=8.8 Hz), 8.36 (1H, dd, J=2.2, 8.8 Hz), 8.51 (1H, d, J=2.2 Hz), 10.98 (1H, s); MS(FAB) m/z: 398 (M+H)+.

Reference： [1]Patent: US2003/134859,2003,A1

27
[ 4845-49-2 ]
[ 57-67-0 ]
N-[amino(imino)methyl]-4-[2-(5-oxo-1,3-diphenyl-1,5-dihydro-4H-pyrazol-4-ylidene)-hydrazino]benzenesulfonamide [ No CAS ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2007,vol. 68,p. 1382 - 1387

28
[ 85-44-9 ]
[ 57-67-0 ]
N-[amino(imino)methyl]-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 3795 - 3799
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3084 - 3087

29
4-nitro-N-(1-azidoformimidoyl)benzenesulfonamide [ No CAS ]
[ 57-67-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5576 - 5592

30
[ 814-68-6 ]
[ 57-67-0 ]
[ 1256381-10-8 ]

Yield	Reaction Conditions	Operation in experiment
	In benzene; at 0℃;Inert atmosphere;	HL monomer was prepared by the reaction of equimolaramounts of AC and sulphaguanidine in dry benzene until the evolution of hydrogen chloride ceased.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2010,vol. 77,p. 795 - 801
[2]Journal of Molecular Structure,2011,vol. 990,p. 26 - 31

31
[ 547-57-9 ]
[ 57-67-0 ]
[ 1312665-64-7 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 5.0 ml of 0.5M hydrochloric acid solution was placed into a 25ml volumetric flask. Then a sample of solution containing 0.4-14.0mugml-1 of sulphanilamide in final volume was added.Next 5.0 ml of 1.25x10-2M sodium nitrite solution was added into the flask. Obtained solution was stirred and cooled on an ice bath(~0 C) for 10 min. Then 1.0 ml of 1.25x10-3M Tropaeolin O solution was added into the flask. Obtained mixture was neutralized by adding of 2.5 ml of 1M sodium hydroxide solution and the pH value was adjusted to pH= 10.5 and distilled water was added to the full volume of 25ml. Then the solution was mixed thoroughly and the absorbance measurements (at room temperature ~20 C) were carried out against all corresponding reagents blank solution at 595nm in 1.0cm cuvettes. Sulphanilamide concentration was calculated using the methods of calibration curve and single-point standardization.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 79,p. 325 - 331

32
[ 642-31-9 ]
[ 57-67-0 ]
[ 1325727-20-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	In ethanol; for 3h;Reflux;	All the chemicals were procured from Sigma-Aldrich, USA.Sulphaguanidine (4-amino-N-[amino(imino)methyl]benzenefulfonamide,0.5 g) and anthracene-9-carbaldehyde (0.48 g) were refluxed in ethanol for 3 h in water bath. The yellow precipitate is filtered off and washed with ethanol and then dried in vacuum.Yield 72%. Elemental analysis: found/calculated (%): C 65.67, 65.00;N 14.2, 13.93; S 8.5, 7.9; H 4.47, 4.47.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 79,p. 1584 - 1592

33
[ 120-14-9 ]
[ 57-67-0 ]
(E)-N-carbamimidoyl-4-((3,4-dimethoxybenzylidene)amino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 3h;Reflux;	All the chemicals were procured from Sigma-Aldrich, USA. 0.5 g of sulphaguanidine and 0.4 g 3,4-dimethoxybenzaldehyde is refluxed in 20 ml ethanol for 3 h and cooled overnight. The white precipitate formed was filtered off, recrystallised from ethanol and dried in vacuum desicator. Elemental analysis: found/calculated (%): C 53.02/53.20; H 4.99/4.89; N 15.50/15.55; S 8.63/8.64; O 17.56/17.55. The FT-IR spectrum (refPreviewPlaceHolderFig. 1) was recorded on a DR/Jasco FT-IR 6300 spectrometer in KBr pellets, number of scans 16, resolution 2 cm-1. The FT-Raman spectrum (refPreviewPlaceHolderFig. 2) was obtained on a BRUKER RFS 100/S, Germany. For excitation of the spectrum the emission of a Nd:YAG laser was used, excitation wavelength 1064 nm, maximal power 150 mW, measurement of solid sample. One thousand scans were accumulated with a total registration time of about 30 min. The spectral resolution after apodization was 2 cm-1.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 84,p. 156 - 163

34
[ 66-77-3 ]
[ 57-67-0 ]
[ 1354658-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 2h;Reflux;	All the chemicals were procured from Sigma-Aldrich, USA. 0.5 mg of sulphaguanidine and 0.3 ml of 1-naphthaldehyde in 20 ml ethanol is refluxed 2 h and cooled. The light yellow precipitate was filtered off, washed with ethanol and dried.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2012,vol. 87,p. 29 - 39

35
[ 123-11-5 ]
[ 57-67-0 ]
(E)-N-carbamimidoyl-4-((4-methoxybenzylidene)amino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 2h;Reflux;	All the chemicals were procured from Sigma-Aldrich, USA. 0.5 mg of sulfaguanidine and 0.3 ml of anisaldehyde in 20 ml ethanol is refluxed 2 h and cooled. The light white precipitate was filtered off, washed with ethanol and dried. Elemental analysis: found/calculated (%): C 54.1/54.19; H 4.7/4.65; N 16.80/16.40; S 9.70/9.91; O 14.35/14.31. The FT-IR spectrum (Fig. 1) was recorded on a DR/Jasco FT-IR 6300 spectrometer in KBr pellets, number of scans 16, resolution 2 cm-1. The FT-Raman spectrum (Fig. 2) was obtained on a BRUKER RFS 100/S, Germany. For excitation of the spectrum the emission of a Nd:YAG laser was used, excitation wavelength 1064 nm, maximal power 150 mW, measurement of solid sample. One thousand scans were accumulated with a total registration time of about 30 min. The spectral resolution afterapodization was 2 cm-1.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2012,vol. 92,p. 84 - 90

36
[ 1379522-28-7 ]
[ 57-67-0 ]
[ 1432024-32-2 ]

Yield	Reaction Conditions	Operation in experiment
52.1%	With acetic acid; for 15h;Reflux;	General procedure: In a flask fitted with a reflux IIa-h (10 mmol) and the corresponding starting aromatic amine (10 mmol) were mixed in an anhydrous acetic acid atmosphere (7 mL). The mixture was boiled for 15 h, cooled to room temperature; 5 mL of light petroleum was added. The precipitated crystals were filtered, washed with ether and dried.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2696 - 2703

37
[ 53384-26-2 ]
[ 57-67-0 ]
[ 1446010-79-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	In 1,4-dioxane; for 3h;Reflux;	General procedure: A mixture of 3 (0.01mol), the appropriate sulfa drugs (namely sulfanilamide, sulfacetanilide, sulfaguanidine, sulfathiazole, sulfapyridine and sulfadiazine) in dioxane (30mL) was heated under reflux for 3h. The solution was concentrated under vacuum, left to cool. The resulting solid was filtered off and recrystallized from diaxone.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 111 - 120

38
[ 346-55-4 ]
[ 57-67-0 ]
[ 1489236-20-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	In N,N-dimethyl-formamide; for 12h;Reflux;	General procedure: A mixture of 1 (2.31 g, 0.01 mol) and the corresponding sulfadrugs (0.012 mol) in dry DMF (20 mL) was refluxed for 12 h. The solid obtained after concentration was filtered and crystallized from dioxane to give 2-14, respectively.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 373 - 383

39
4-isothiocyanato-7-(triflouromethyl)quinoline [ No CAS ]
[ 57-67-0 ]
[ 1491007-07-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine; In N,N-dimethyl-formamide; for 24h;Reflux;	General procedure: A mixture of 18 (0.43 g, 0.001 mol) and the appropriate sulfadrugs (0.0012 mol) in dry DMF (30 mL) containing a catalytic amount of triethylamine was heated under reflux for 24 h. The obtained solid was filtered and crystallized from dioxane to give 19-30, respectively.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 373 - 383

40
[ 50329-91-4 ]
[ 57-67-0 ]
N-carbamimidoyl-4-((4-chloro-2-oxo-2H-chromen-3-yl)methyleneamino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In ethanol; acetic acid; at 20℃; for 3h;	General procedure: To a solution of compounds 4a-4c (7.6 mmol) in ethanol (15 mL) was added different substituted sulfonamide (7.6 mmol) and acetic acid (0.5 mL). The mixture was heated at room temperature for 3 h. A solid product was immediately formed which was filtered, washed with water. And the crude products were purified by recrystallization with ethanol, ethyl acetate and acetone(1:1:0.5) washed by ice-water (25 mL) for three times and dried to give a yellow solid product 5a-5r.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 66,p. 1 - 11

41
[ 51069-84-2 ]
[ 57-67-0 ]
N-carbamimidoyl-4-((4-chloro-6-methyl-2-oxo-2H-chromen-3-yl)methylene-amino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	In ethanol; acetic acid; at 20℃; for 3h;	General procedure: To a solution of compounds 4a-4c (7.6 mmol) in ethanol (15 mL) was added different substituted sulfonamide (7.6 mmol) and acetic acid (0.5 mL). The mixture was heated at room temperature for 3 h. A solid product was immediately formed which was filtered, washed with water. And the crude products were purified by recrystallization with ethanol, ethyl acetate and acetone(1:1:0.5) washed by ice-water (25 mL) for three times and dried to give a yellow solid product 5a-5r.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 66,p. 1 - 11

42
6, 8-ditertbutyl-4-chloro-2-oxo-2H-chromene-3-carbaldehyde [ No CAS ]
[ 57-67-0 ]
N-carbamimidoyl-4-((6,8-di-tert-butyl-4-chloro-2-oxo-2H-chromen-3-yl)methyleneamino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol; acetic acid; at 20℃; for 3h;	General procedure: To a solution of compounds 4a-4c (7.6 mmol) in ethanol (15 mL) was added different substituted sulfonamide (7.6 mmol) and acetic acid (0.5 mL). The mixture was heated at room temperature for 3 h. A solid product was immediately formed which was filtered, washed with water. And the crude products were purified by recrystallization with ethanol, ethyl acetate and acetone(1:1:0.5) washed by ice-water (25 mL) for three times and dried to give a yellow solid product 5a-5r.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 66,p. 1 - 11

43
[ 444731-74-2 ]
[ 57-67-0 ]
[ 1572439-40-7 ]

Reference： [1]Chemical Biology and Drug Design,2014,vol. 83,p. 306 - 316

44
[ 444731-75-3 ]
[ 57-67-0 ]
[ 1572439-44-1 ]

Reference： [1]Chemical Biology and Drug Design,2014,vol. 83,p. 306 - 316

45
[ 1175005-61-4 ]
[ 57-67-0 ]
N-carbamimidoyl-4-(4-(2-(2-methyl-5-nitro-1H-imidazole-1-yl)-ethoxy)benzylideneamino)benzenesulfonamide [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 33029 - 33038

46
3-(2-(2-methyl-5-nitro-1-imidazole)ethoxy)benzaldehyde [ No CAS ]
[ 57-67-0 ]
N-carbamimidoyl-4-(3-(2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy)benzylideneamino)benzenesulfonamide [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 33029 - 33038

47
[ 41167-60-6 ]
[ 57-67-0 ]
N-[4-(carbamimidoylsulfamoyl)phenyl]-2-hydroxy-4-oxo-4-(4-fluorophenyl)but-2-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium acetate; acetic acid; for 0.333333h;Reflux;	General procedure: A solution of 0.01 mol of methyl 4-brombenzoylpyruvate and 0.01 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added to a solution of 0.01 mol of 4-aminobenzenesulfonylguanidine in 15 mL of glacial acetic acid. The reaction mixture was refluxed for 20 min. The precipitate was filtered off uponcooling and recrystallized from a mixture of acetic acid-dioxane (1 : 1).

Reference： [1]Russian Journal of Organic Chemistry,2014,vol. 50,p. 1692 - 1694
Zh. Org. Khim.,2014,vol. 50,p. 1703 - 1705,3
[2]Russian Journal of General Chemistry,2015,vol. 85,p. 833 - 836
Zh. Obshch. Khim.,2015,vol. 85,p. 588 - 591,4

48
[ 77303-35-6 ]
[ 57-67-0 ]
[ 149-73-5 ]
C₁₅H₁₄N₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In N,N-dimethyl-formamide; for 0.0333333h;Heating;	General procedure: A mixture of 150 mg (1 mmol) of 4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile 1, 0.09 ml (1 mmol) ofaniline and 0.1 ml (1 mmol) of trimethyl orthoformate was heated in0.3 ml DMF for 2 min. The yellow precipitate was filtered off and washedwith DMF to give 0.24 g of (Z)-4-methyl-2,6-dioxo-5-(phenylaminomethylidene)-1,2,5,6-tetrahydropyridine-3-carbonitrile 4a. Yield 94%

Reference： [1]Mendeleev Communications,2015,vol. 25,p. 133 - 134

49
[ 39848-01-6 ]
[ 57-67-0 ]
2-hydroxy-4-(4-methylphenyl)-4-oxo-2-butenoic acid N-(4-guanidylsulfonylphenyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium acetate; acetic acid; for 0.333333h;Reflux;	General procedure: A solution of 0.01 mol of methyl 4-brombenzoylpyruvate and 0.01 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added to a solution of 0.01 mol of 4-aminobenzenesulfonylguanidine in 15 mL of glacial acetic acid. The reaction mixture was refluxed for 20 min. The precipitate was filtered off uponcooling and recrystallized from a mixture of acetic acid-dioxane (1 : 1).

Reference： [1]Russian Journal of General Chemistry,2015,vol. 85,p. 833 - 836
Zh. Obshch. Khim.,2015,vol. 85,p. 588 - 591,4

50
[ 57-67-0 ]
(2E,5Z)-2-Hydroxy-4-oxo-6-phenyl-hexa-2,5-dienoic acid methyl ester [ No CAS ]
2-hydroxy-4-oxo-6-phenylhex-2,5-dienoic acid N-(4-guanidylsulfonylphenyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium acetate; acetic acid; for 0.333333h;Reflux;	General procedure: A solution of 0.01 mol of methyl 4-brombenzoylpyruvate and 0.01 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added to a solution of 0.01 mol of 4-aminobenzenesulfonylguanidine in 15 mL of glacial acetic acid. The reaction mixture was refluxed for 20 min. The precipitate was filtered off uponcooling and recrystallized from a mixture of acetic acid-dioxane (1 : 1).

Reference： [1]Russian Journal of General Chemistry,2015,vol. 85,p. 833 - 836
Zh. Obshch. Khim.,2015,vol. 85,p. 588 - 591,4

51
[ 57-67-0 ]
methyl 4-(4-ethoxyphenyl)-2-hydroxy-4-oxobut-2-enoate [ No CAS ]
2-hydroxy-4-(4-ethoxyphenyl)-4-oxo-2-butenoic acid N-(4-guanidylsulfonylphenyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium acetate; acetic acid; for 0.333333h;Reflux;	General procedure: A solution of 0.01 mol of methyl 4-brombenzoylpyruvate and 0.01 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added to a solution of 0.01 mol of 4-aminobenzenesulfonylguanidine in 15 mL of glacial acetic acid. The reaction mixture was refluxed for 20 min. The precipitate was filtered off uponcooling and recrystallized from a mixture of acetic acid-dioxane (1 : 1).

Reference： [1]Russian Journal of General Chemistry,2015,vol. 85,p. 833 - 836
Zh. Obshch. Khim.,2015,vol. 85,p. 588 - 591,4

52
[ 65356-50-5 ]
[ 57-67-0 ]
4-(4-bromophenyl)-2-hydroxy-4-oxo-2-butenoic acid N-(4-guanidylsulfonylphenyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium acetate; acetic acid; for 0.333333h;Reflux;	A solution of 0.01 mol of methyl 4-brombenzoylpyruvate and 0.01 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added to a solution of 0.01 mol of 4-aminobenzenesulfonylguanidine in 15 mL of glacial acetic acid. The reaction mixture was refluxed for 20 min. The precipitate was filtered off uponcooling and recrystallized from a mixture of acetic acid-dioxane (1 : 1).

Reference： [1]Russian Journal of General Chemistry,2015,vol. 85,p. 833 - 836
Zh. Obshch. Khim.,2015,vol. 85,p. 588 - 591,4

53
[ 39848-02-7 ]
[ 57-67-0 ]
2-hydroxy-4-(4-methoxyphenyl)-4-oxo-2-butenoic acid N-(4-guanidylsulfonylphenyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium acetate; acetic acid; for 0.333333h;Reflux;	General procedure: A solution of 0.01 mol of methyl 4-brombenzoylpyruvate and 0.01 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added to a solution of 0.01 mol of 4-aminobenzenesulfonylguanidine in 15 mL of glacial acetic acid. The reaction mixture was refluxed for 20 min. The precipitate was filtered off uponcooling and recrystallized from a mixture of acetic acid-dioxane (1 : 1).

Reference： [1]Russian Journal of General Chemistry,2015,vol. 85,p. 833 - 836
Zh. Obshch. Khim.,2015,vol. 85,p. 588 - 591,4

54
[ 96-50-4 ]
[ 57-67-0 ]
2-amino-5-[4-(carbamimidoylsulfamoyl)phenyl]azo}thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogenchloride; sodium acetate; sodium nitrite; In ethanol; water; at 0 - 5℃; for 2h;	General procedure: A solution of aryl diazonium chloride was prepared by adding cold sodium nitrite solution (0.7 gin 10 mL H2O) to a cold suspension of aryl amine 2 and/or 3 (0.01 mol) in 3 mL concentrated HCl withstirring. The freshly prepared solution was added with continuous stirring to a cold solution (0-5 C) of 2-aminothiazole 1 (1 g, 0.01 mol) in 30 mL ethanol and 4.0 g sodium acetate. The reaction mixture was stirred at 0-5 C for 2 h, diluted with water, and the products collected by filtration. The obtained 2-amino-5-arylazothiazoles 4-7 were dried and recrystallized from ethanol. 2-Amino-5-[4-(carbamimidoyl-sulfamoyl)-phenyl]azo}thiazole (4). Red solid, yield 74%, m.p. 220-221 C. IR (KBr, cm-1): 3432, 3312, 3177 (NH2 and NH), 1640 (C=N). 1H-NMR (DMSO-d6, delta ppm): 7.05 (t,1H, J = 7.15 Hz, NH), 7.59 (d, 2H, J = 7.80 Hz, Ar-H), 7.97 (d, 2H, J = 7.80 Hz, Ar-H), 8.36 (s, 1H, C-4thiazole-H), 8.65 (d, 2H, J = 8.50 Hz, NH2), 9.40 (s, 2H, NH2), 11.35 (s, 1H, NH). 13C-NMR (DMSO-d6, delta ppm): 121.99 (2C), 129.51 (2C), 139.79, 144.88, 152.80, 155.20, 158.91, 173.40. Anal. Calcd. forC10H11N7O2S2 (325.37): C, 36.91; H, 3.41; N, 30.13,Found: C, 36.83; H, 3.45; N, 30.20.

Reference： [1]Molecules,2016,vol. 21

55
[ 6484-25-9 ]
[ 57-67-0 ]
N-carbamimidoyl-4-(2-phenylquinazolin-4-ylamino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In N,N-dimethyl-formamide; for 22h;Reflux;	General procedure: A mixture of 4-chloro-2-phenylquinazoline (1, 2.42 g, 0.01 mol) and sulfonamides (0.012 mol) in dry dimethylformamide (10 mL) was refluxed for 22 h., then left to cool. The solid product formed upon pouring onto ice/water was collected by filtration and recrystallized from ethanol-dimethylformamide to give 2-18, respectively.

Reference： [1]Molecules,2016,vol. 21

56
[ 33987-02-9 ]
[ 57-67-0 ]
4-(benzo[g]quinazolin-4-ylamino) N-carbamimidoylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine; In N,N-dimethyl-formamide; for 24h;Reflux;	General procedure: A mixture of 4-chlorobenzo[g]quinazoline 1 (2.15g, 0.01mmol) and sulfonamides (0.012 mmol) in dry DMF (15mL)was refluxed for 24h., then left to cool. The solid productformed upon pouring onto ice/ water was collected by filtrationand recrystallized from ethanol- DMF to give 2-18, respectively.

Reference： [1]Medicinal Chemistry,2016,vol. 12,p. 448 - 456

57
[ 28900-10-9 ]
[ 57-67-0 ]
N-carbamimidoyl-4-(3-cyano-6-methylpyridin-2-ylamino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In N,N-dimethyl-formamide; for 18h;Reflux;	General procedure: A mixture of <strong>[28900-10-9]2-chloro-6-methylnicotinonitrile</strong> (II)(1.52 g, 0.01 mol) and corresponding sulfonamide derivatives (0.012 mol) in dry dimethylformamide(10 mL) containing 3 drops of trimethylamine was refluxed for 18 h then left to cool. The solid productformed upon pouring onto ice water was collected byfiltration and recrystallized from ethanol-dimethylformamide to give (III-XX), respectively.

Reference： [1]Russian Journal of Bioorganic Chemistry,2016,vol. 42,p. 441 - 448

58
4-chloro-5-(4-chlorophenyl)thieno[2,3-d]pyrimidine [ No CAS ]
[ 57-67-0 ]
N-carbamimidoyl-4-[5-(4-chlorophenyl)thieno[2,3-d]pyrimidin-4-yl]amino}benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With pyridine;Reflux;	General procedure: A stirred mixture of either thieno[2,3-d] pyrimidine 1aor b(1 mmol) and the appropriate sulfonamide derivative (1.2 mmol) in dry pyridine (for compounds 3band i) or isopropanol (for the rest of compounds) (20 mL) was heated under reflux for 18-24 h. The reaction mixture was cooled and the formed solid was filtered, dried and crystallized from the appropriate solvent.

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 1172 - 1180

59
4-chloro-5-(4-nitrophenyl)thieno[2,3-d]pyrimidine [ No CAS ]
[ 57-67-0 ]
N-carbamimidoyl-4-[5-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4-yl]amino}benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With pyridine;Reflux;	General procedure: A stirred mixture of either thieno[2,3-d] pyrimidine 1aor b(1 mmol) and the appropriate sulfonamide derivative (1.2 mmol) in dry pyridine (for compounds 3band i) or isopropanol (for the rest of compounds) (20 mL) was heated under reflux for 18-24 h. The reaction mixture was cooled and the formed solid was filtered, dried and crystallized from the appropriate solvent.

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 1172 - 1180

60
[ 13250-46-9 ]
[ 57-67-0 ]
N-((4-(N-carbamimidoylsulfamoyl)phenyl)carbamothioyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone; for 2h;Reflux;	General procedure: A solution of acyl chloride (5mmol) and potassium thiocyanate (5.5mmol) in acetone (20mL) was reacted under reflux for 1h. Aromatic amine (5mmol) was added and the mixture was stirred under reflux for 2h. The reaction mixture was cooled to room temperature. The precipitate was filtered, washed with water and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 229 - 236

61
[ 708-06-5 ]
[ 57-67-0 ]
(E)-N-(diaminomethylene)-4-(((2-hydroxynaphthalen-1-yl)methylene) amino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol; for 2.5h;Reflux;	General procedure: 2-(Hydroxy)naphthaldehyde (0.2 g, 1.16 mmol) was dissolved in 25 ml of super dry ethanol followed by the dropwise addition of sulfathiazole (STZ) (0.3 g, 1.18 mmol in 10 ml ethanol) with constant stirring for 30 min. The mixture was then refluxed for 2.5 h. The solution was then cooled to room temperature and allowed to evaporate slowly in air; an orange coloured crystals of (E)-4-(((2-hydroxynaphthalen-1-yl)methylene)amino)-N-(thiazol-2-yl)benzenesulfonamide (1a) deposited on the wall of the beaker. The crystals were filtered and further recrystallized from hot ethanol. The purity of the product was checked by TLC; yield, 0.32 g (66%).

Reference： [1]Journal of Molecular Structure,2017,vol. 1127,p. 557 - 567

62
ethyl 3-(4-chlorophenyl)-4-isothiocyanato-1H-pyrazol-5-carboxylate [ No CAS ]
[ 57-67-0 ]
ethyl 3-(4-chlorophenyl)-N-carbamimidoylbenzenesulfonamido-4-thioureido-1H-pyrazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In N,N-dimethyl-formamide; for 4h;Reflux;	General procedure: A mixture of compound 11 (3.07 g, 10 mmol) and sulfa drugs (10 mmol) in DMF (30 mL) wasstirred under reflux for 4 h. The reaction mixture was poured onto ice water and the obtained productwas recrystallized from dioxane to give compounds 12a-d, respectively.

Reference： [1]Molecules,2016,vol. 21

63
[ 613-94-5 ]
[ 4637-24-5 ]
[ 57-67-0 ]
N-carbamimidoyl-4-(3-phenyl-4H-1,2,4-triazol-4-yl) benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With acetic acid; In acetonitrile; for 9h;Reflux;	General procedure: A mixture of benzoylhydrazine (1.22 g, 0.01mol), dimethylformamide-dimethylacetal (1.91 g,0.01 mol)) and sulfa-drugs (0.012 mol) in dry acetonitrile(15 mL) containing acetic acid (3 mL) was refluxed for 9 h., then left to cool. The solid product formed was collected by filtration and recrystallized from dioxane to give compounds 1-13, respectively.

Reference： [1]Acta poloniae pharmaceutica,2016,vol. 73,p. 1147 - 1153

64
[ 57-67-0 ]
[ 371756-61-5 ]
(Z)-N-carbamimidoyl-4-(3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-enylamino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In ethanol; for 21h;Reflux;	General procedure: 5.1.2.1. General procedure. A mixture of 2 (1.88 g, 0.01 mol) and sulfa-drugs (0.012 mol) in absolute ethanol (10 mL) and glacial acetic acid (5 mL) was refluxed for 21 h, then left to cool. The solid product formed was collected by filtration and recrystallized from ethanol-dimethylformamide to give 3-20.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 946 - 958

65
[ 4008-48-4 ]
[ 57-67-0 ]
C₁₆H₁₃N₇O₅S [ No CAS ]

Reference： [1]Applied Organometallic Chemistry,2016,vol. 30,p. 664 - 673

66
[ 127172-22-9 ]
[ 57-67-0 ]
Z-N-carbamimidoyl-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With acetic acid; In ethanol; for 22h;Reflux;	General procedure: General ProcedureA mixture of 2 (2.35 g, 0.01 mol) and sulfa drugs (0.012 mol) in absolute ethanol (10 mL) and glacial acetic acid (5 mL) was refluxed for 22h, and subsequently left to cool. The solid product formed was collected by filtration and recrystallized from acetic acid to give compounds 3-19.

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 1747 - 1754

67
[ 100753-41-1 ]
[ 57-67-0 ]
C₂₆H₂₈N₄O₆S [ No CAS ]
4-amino-N-(4-(2,4-dimethoxyphenyl)-6-(3,4-dimethoxyphenyl)pyrimidin-2-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 4-amino-N-(aminoiminomethyl-benezenesulfonamide) (2.000 g, 9.33 mmol) and sodium isopropoxide (1.607 g, 19.60 mmol) in isopropanol (50 mL) was stirred for 30 min. To this mixture was then added 8 (2.74 g, 8.34 mmol) portion wise over 20 min. the mixture was heated at reflux overnight. The resulting crude mixture was concentrated in vacuo, dissolved in ethyl acetate (200 mL) and washed with 1M HCl (200 mL) and saturated NaCl (200 mL). The organic layer was then separated, dried over Mg2SO4, concentrated under vacuum and the resulting mixture of (3.3:7.7; calculated by 1H NMR) pyrimidine 9 and dihydropyrimidine 10 were then carried through with no further purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 162 - 167

68
[ 100753-41-1 ]
[ 57-67-0 ]
4-amino-N-(4-(2,4-dimethoxyphenyl)-6-(3,4-dimethoxyphenyl)pyrimidin-2-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		A solution of 4-amino-N-(aminoiminomethyl-benezenesulfonamide) (2.000 g, 9.33 mmol) and sodium isopropoxide (1.607 g, 19.60 mmol) in isopropanol (50 mL) was stirred for 30 min. To this mixture was then added 8 (2.74 g, 8.34 mmol) portion wise over 20 min. the mixture was heated at reflux overnight. The resulting crude mixture was concentrated in vacuo, dissolved in ethyl acetate (200 mL) and washed with 1M HCl (200 mL) and saturated NaCl (200 mL). The organic layer was then separated, dried over Mg2SO4, concentrated under vacuum and the resulting mixture of (3.3:7.7; calculated by 1H NMR) pyrimidine 9 and dihydropyrimidine 10 were then carried through with no further purification. To the above mixture of pyrimidine 9 and dihydropyrimidine 10 in anhydrous CH2Cl2 (200 mL) was added pyridinium dichromate (5.76 g, 15.30 mmol) in a single batch. The reaction mixture was then purged with nitrogen and the mixture was stirred at room temperature for 16 h under a N2 atmosphere. The resulting mixture was then adsorbed to silica and subjected to silica gel column chromatography (1% CH3OH in CH2Cl2) to afford a yellow solid (2.830 g, 34% over 2-steps); MP >234 C (dec.). 1H NMR (400 MHz, acetone-d6) delta 9.75 (bs, 1H), 8.11-8.09 (m, 2H), 7.87 (d, J = 8.6 Hz, 2H), 7.81 (d, J = 1.4 Hz, 1H), 7.72 (dd, J = 8.3, 1.3 Hz, 1H), 7.08 (d, J = 8.4 Hz, 1H), 6.73 -6.68 (m, 4H), 5.45 (s, 2H), 3.98-3.90 (m, 12H); 13C NMR (101 MHz, DMSO-d6) delta 163.5, 163.2, 162.6, 159.4, 157.2, 152.9, 151.3, 148.8, 131.8, 129.5, 129.0, 125.5, 120.3, 118.0, 112.1, 111.7, 110.1, 109.6, 105.8, 98.7, 55.9, 55.6, 55.5; LCMS (APCI+) m/z: 523 (M+H, 100%), 524(25), 525(13).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 162 - 167

69
[ 542-78-9 ]
[ 57-67-0 ]
[ 68-35-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium methylate; In methanol; at 65℃; for 2h;	A mixing 8.6 g NH4Cl and 23. lg (NH4) 2C03 in a certain ratio, Adding activated carbon catalyst, Then add 32g of dicyandiamide heated to melt at 150 C for 30min; B To join the above Rong melt liquid 80g p-aminosulfonamide, 70g sodium carbonate continue to melt financial, in 25min heated to 150 C, to maintain 30min; C To the mixture obtained in step B, 400 ml of boiling water was added and the mixture was stirred well. The resulting suspension was cooled to 40 C and filtered to obtain crude sulfanilamide. To the flask, 93 g of a 25% methanol solution of sodium methoxide, 33 g of crude sulfanilamide, Stirring to join malondialdehyde 13. 5g, heating to 65 C, reaction 2h, Complete ring condensation reaction, recovery of methanol after sulfadiazine crude. Add 200ml of water to the crude, heating, saturated with hydrogen peroxide to adjust the pH to 9. 5, after the whole solution, add 20g of activated carbon, heat decolorization at 80 C. Filtration, the filtrate added ? 5g ammonium chloride, with 10% acetic acid to adjust the pH to 5.2. Precipitation crystal, cold after filtration, washing, drying Of the sulfadiazine quality, yield 89%, purity of 98.0%.

Reference： [1]Patent: CN105254575,2016,A .Location in patent: Paragraph 0015-0016

70
[ 127099-85-8 ]
[ 63-74-1 ]
[ 57-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium carbonate; sodium carbonate; pyrographite; ammonium chloride; at 150℃; for 30h;	A 8.6g NH4Cl and 23. lg (NH4) 2C03 in accordance with a certain percentage of mixing, Adding activated carbon catalyst, Then add 32g of dicyandiamide heated to melt at 150 C for 30min; B To join the above Rong melt liquid 80g p-aminosulfonamide, 70g sodium carbonate continue to melt financial, in 25min heated to 150 C, to maintain 30min; C To the mixture obtained in step B, 400 ml of boiling water was added and the mixture was stirred well. The resulting suspension was cooled to 40 C and filtered to obtain crude sulfanilamide. To the flask, 93 g of a 25% methanol solution of sodium methoxide, 33 g of crude sulfanilamide, Stirring to join malondialdehyde 13. 5g, heating to 65 C, reaction 2h, Complete ring condensation reaction, recovery of methanol after sulfadiazine crude. Add 200ml of water to the crude, heating, saturated with hydrogen peroxide to adjust the pH to 9. 5, after the whole solution, add 20g of activated carbon, heat decolorization at 80 C. Filtration, the filtrate added ? 5g ammonium chloride, with 10% acetic acid to adjust the pH to 5.2. Precipitation crystal, cold after filtration, washing, drying Of the sulfadiazine quality, yield 89%, purity of 98.0%.

Reference： [1]Patent: CN105254575,2016,A .Location in patent: Paragraph 0015-0016

71
[ 65356-50-5 ]
[ 57-67-0 ]
methyl (2E)-4-(4-bromophenyl)-2-[4-(carbamimidoylsulfamoyl)phenyl]amino}-4-oxobut-2-enoate [ No CAS ]
methyl (2Z)-4-(4-bromophenyl)-2-[4-(carbamimidoylsulfamoyl)phenyl]amino}-4-oxobut-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In ethanol; for 0.0833333h;Reflux;	4-Amino-N-carbamimidoylbenzene-1-sulfonamide, 2.32 g (0.01 mol), was dissolved on heating in 15 mL of glacial acetic acid, a solution of 2.85 g (0.01 mol) of methyl 4-(4-bromophenyl)-2-hydroxy-4oxobut-2-enoate in 15 mL of ethanol was added, and the mixture was refluxed for 5 min. After cooling, the precipitate was filtered off and recrystallized from acetic acid-ethanol (1 : 1). Yield 3.46 g (72%), mp 151-153C. IR spectrum, nu, cm-1: 3448, 3410, 3360, 3256 (NH2, NH), 1744 (C=O, ester), 1628 (4-C=O), 1312, 1140 (SO2). 1H NMR spectrum, delta, ppm: 3.78 s (3H, CH3O), 6.51 s (1H, 3-H), 6.64 s [4H, NHC(=NH)NH2], 7.03-7.90 m (8H, Harom), 9.97 s (0.1H, NH, E), 11.62 s (0.9H, NH, Z). Found, %: C 44.79; H 3.52; N 11.70; S 6.57. C18H17BrN4O5S. Calculated, %: C 44.92; H 3.56; N 11.64; S 6.62.